Winchester College, The King's Medal
Winchester College Archives states-He was the elder son of Thomas Paterson Gillespie of Longcroft, Linlithgow and elder brother of Lieutenant Thomas Cunningham Gillespie (K. 1905-1911), King's Own Scottish Borderers, who fell on October 18th 1914 (see individual entry). He entered College from Cargilfield School, Edinburgh, became Prefect of Chapel and won the King's Gold Medal for Latin Verse, the King's Silver Medal for Latin Speech, the Warden and Fellow's Prizes for Greek Prose and Latin Essay and the Duncan Prize for Reading. In his last year he played in College XV. He was elected in 1908 to a Scholarship at New College, Oxford, and took his degree in 1912 with a First Class in Classical Moderations and a Second in Literae Humanitores.
He was reading for the Bar when war broke out, and volunteered his services at once, obtaining a commission in the 2nd Battalion Argyll and Sutherland Highlanders. He went to the front in February 1915, spending the evening of 20th February at Winchester College. "Hutchie (2nd Lieutenant R.H. Hutchinson, 8th Black Watch, Coll.1903-1909, killed in action October 1915 " and I had a very cheerful dinner with the Headmaster." The sector in which his Battalion found itself was quite quiet and he had the time to write many letters home. His most famous letter, published after his death in the Wykehamist of 14th June 1915 was written to his Headmaster and it was subsequently picked up by the national press for its vision of what might be done with the Western Front after the War. He visited friends in other units; the mother of one of his best friends, Isaac Bayley Balfour (killed in action at Gallipoli; see individual entry), sent him a book on botany and he even managed to grow flowers from seeds sent from home.
He went into the attack at Cuinchy on 25th September 1915 as part of the first day of the Battle of Loos, and was killed while leading a charge against an enemy position: he fell as he reached the German trenches. According to survivors, he was the only officer to get that far. With no known grave he is commemorated on Panels 125-127 of the Loos Memorial.
A volume of his letters entitled "Letters from Flanders" was published by Smith, Elder, in 1916. It contains a brief memoir of both brothers by the Bishop of Oxford, the Rt Rev. Hubert Burge, Headmaster of the College during Gillespie's time. In it Alexander Gillespie describes his search for the chateau where Tom spent his last night before going into action and his reaction to the news of his death.
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